Ethylation of 5-acetyl-5-methyl-7-phenyl-4,7-dihydro[1,2,4]triazolo[1,5-a]pyrimidine
Abstract
Alkylation of 5‑acetyl-5-methyl-7-phenyl-4,7-dihydro[1,2,4]triazolo[1,5-a]pyrimidine with ethyl bromide in heterogeneous system КОН–H2O–MeCN leads to the formation of the mixture of two isomers. The structures of the latter were elucidated by NOE experiment. Recrystallization of the obtained mixture from EtOAc results in the major product of alkylation, 5‑acetyl-4-ethyl-5-methyl-7-phenyl-4,7-dihydro[1,2,4]triazolo[1,5‑a]pyrimidine.
Downloads
References
Chebanov V.A., Gura K.A., Desenko S.M. // Top. Heterocycl. Chem. – 2010. – 23. – P. 41–84.
Sedash Yu.V., Gorobets N.V., Chebanov V.A., Konovalova I.S., Shishkin O.V.,
Desenko S.M. // RSC Adv. – 2012. – 2, № 17. – P. 6719–6728.
Gorobets N.V., Sedash Yu.V., Ostras K.S., Zaremba O.V., Shishkina S.V., Baumer V.N., Shishkin O.V., Kovalenko S.M., Desenko S.M., Van der Eycken E.V. // Tetrahedron Lett. – 2010. – 51. – P. 2095–2098.
Kumari K., Raghuvanshi D. S., Singh K.N. // Org. Prep.Proced. Intern. – 2012. – 44. – P. 460–466.
Desenko S.M., Komykhov S.A., Orlov V.D. // J. Het. Chem. – 1998. – 35. – P. 989–990.
Lipson V.V., Desenko S.M., Ignatenko I.V., Shishkin O.V., Shishkina S.V. // Russ. Chem. Bull. – 2006. – 55, № 2. – P. 345–350.
Füller H., Hauschild F, Modersohn D, Thomas E. // Pharmazie. – 1971. – 26. – P. 554–562.
Kolosov M.A., Orlov V.D., Vashchenko V.V., Shishkina S.V., Shishkin O.V. // Collect. Czech. Chem. Commun. – 2007. – 72, № 9. – Р. 1219–1228.
Ханина Е.Л., Андабурская М.Б., Дубур Г.Я., Золотоябко Р.М. // Изв. АН Латв. ССР. – 1978. – 44, № 2. – С. 197–200.
Desenko S.M., Orlov V.D., Lipson V.V. // Chem. Het. Comp. – 1990. – 26, № 12. – P. 1362–1366.
Allen J., Bourbeau M., Wohlhieter G. // J. Med. Chem. – 2009. – 52, № 22. – P. 7044–7053.
Beck H., Degraffenreid M., Fox B. // Bioorg. Med. Chem. Lett. – 2011. – 11, № 9. – P. 2752–2755.
Desenko S.M., Komykhov S.A., Orlov V.D., Meier H. // J. Heterocycl. Chem. – 1998. – № 4. – P. 989–990.